EP2273966A1 - Utilisation de copolymères blocs de siloxane organomodifiés pour produire des compositions cosmétiques ou pharmaceutiques - Google Patents

Utilisation de copolymères blocs de siloxane organomodifiés pour produire des compositions cosmétiques ou pharmaceutiques

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Publication number
EP2273966A1
EP2273966A1 EP09745639A EP09745639A EP2273966A1 EP 2273966 A1 EP2273966 A1 EP 2273966A1 EP 09745639 A EP09745639 A EP 09745639A EP 09745639 A EP09745639 A EP 09745639A EP 2273966 A1 EP2273966 A1 EP 2273966A1
Authority
EP
European Patent Office
Prior art keywords
emulsifier
emulsion
oil
cosmetic
general formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP09745639A
Other languages
German (de)
English (en)
Other versions
EP2273966B1 (fr
Inventor
Jürgen Meyer
Frank Unger
Michael Ferenz
Sascha Herrwerth
Christian Hartung
Andrea Lohse
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Evonik Operations GmbH
Original Assignee
Evonik Goldschmidt GmbH
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Filing date
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Application filed by Evonik Goldschmidt GmbH filed Critical Evonik Goldschmidt GmbH
Publication of EP2273966A1 publication Critical patent/EP2273966A1/fr
Application granted granted Critical
Publication of EP2273966B1 publication Critical patent/EP2273966B1/fr
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/373—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicones
    • C11D3/3738—Alkoxylated silicones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/895—Polysiloxanes containing silicon bound to unsaturated aliphatic groups, e.g. vinyl dimethicone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/04—Drugs for skeletal disorders for non-specific disorders of the connective tissue
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/44—Block-or graft-polymers containing polysiloxane sequences containing only polysiloxane sequences
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/04—Preparations for care of the skin for chemically tanning the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations

Definitions

  • organomodified siloxane block copolymers for the preparation of cosmetic or pharmaceutical compositions
  • the invention relates to emulsifier systems comprising organomodified siloxane block copolymers, as well as to cosmetic, dermatological or pharmaceutical formulations containing these emulsifier systems.
  • Organomodified siloxanes are used in a wide variety of applications. Their properties can be adjusted, among other things, by the type of modification as well as by the modification density.
  • organophilic or nonionic hydrophilic groups can be attached to a siloxane backbone.
  • Such compounds are used, for example, as polyurethane foam stabilizers, as defoamers in fuels or as additives in paints and coatings.
  • DE 102005001041 describes functionalized polyorganosiloxanes and their use as fuel defoamers.
  • the allyl polyethers in the siloxanes represented herein may be replaced by modification of the hydrocarbon radical synthesis.
  • siloxanes can be linked by reaction with, for example, ⁇ -olefins with hydrophobic groups.
  • the silicone waxes thus obtained serve, for example, as an additive in personal care applications.
  • Suitable as a cosmetic emulsifier are, for example, siloxanes which carry not only aliphatic groups based on ⁇ -olefins polyether.
  • a typical example of this is the sales product ABIL EM 90 from Evonik Goldschmidt GmbH (Germany), which is characterized in particular by excellent stabilization of water-in-oil (W / O) emulsions.
  • Siloxane-based emulsifiers for oil-in-water (O / W) emulsions must have a more hydrophilic character, which is why these products are generally pure polyethersiloxanes.
  • EP 1125574 describes the use of relatively hydrophobic polyether siloxanes as O / W emulsifiers in which the polyether groups are ⁇ - ⁇ or terminal siloxane backbones. These structures are characterized in particular by a velvety silky feel on the skin, which they are able to incorporate into cosmetic emulsions.
  • a disadvantage of the use of these structures is often insufficient emulsifying ability.
  • EP0298402 describes the use of organopolysiloxane-polyoxyalkylenes as emulsifier in water-in-oil emulsions and represents the known, the closest prior art.
  • the organopolysiloxane-polyoxyalkylenes are characterized in that two organopolysiloxane-polyoxyalkylene molecules are connected to one another via a shortest, non-hydrolyzable crosslinkers.
  • the molar ratio of vinylic crosslinker to organopolysiloxane-polyoxyalkylene linker molecules is very large. This leads to unfavorable by-products. For this reason too, among others, the emulsifier systems described in EP0298402 are only of limited use for cosmetic applications.
  • O / W as well as in W / O emulsions can be used and in particular in O / W emulsions are able to combine a velvety-silky skin feel with outstanding emulsifying properties.
  • siloxanes should preferably be easy to process (liquid at room temperature) and combined with conventional siloxanes in formulations.
  • organomodified siloxane block copolymers prepared by a process described in claim 1 powerful emulsifiers, especially for cosmetic, dermatological or pharmaceutical formulations represent, which are able to solve this problem.
  • the invention therefore relates to emulsifier systems which contain organomodified siloxane block copolymers prepared by a process described in claim 1.
  • a particular advantage of the emulsifier systems according to the invention are their outstanding emulsifying and stabilizing properties.
  • Another advantage is that they make it possible to apply a velvety-silky feel to the skin in cosmetic formulations. This is important because consumers increasingly value cosmetic
  • Formulations are not only easy to disperse and penetrate the skin, but leave a smooth, soft, velvety appearance after retraction.
  • a further advantage of the emulsifier systems according to the invention is that the properties of laterally modified siloxanes and of ⁇ , ⁇ -modified siloxanes are combined in them, and thus a higher degree of modification in terms of a greater number of substitution options is given.
  • emulsifier systems are described below by way of example, without the invention being restricted to these exemplary embodiments.
  • ranges, general formulas, or classes of compounds are intended to encompass not only the corresponding regions or groups of compounds explicitly mentioned, but also all sub-regions and sub-groups of compounds obtained by removing individual values (ranges) or compounds can be. If documents are cited in the context of the present description, then their Contents fully belong to the disclosure of the present invention. If, in the context of the present invention, compounds such as, for example, organomodified polysiloxanes, are described which may have different units in multiple units, these may be random (statistical oligomer) or ordered
  • an emulsifier system is an emulsifier which contains at least one substance of the general formula (I) and, if appropriate, at least one co-emulsifier.
  • the invention therefore relates to emulsifier systems containing organomodified siloxane block copolymers which have been prepared by
  • R 1 is the same or different, branched or unbranched, aliphatic or aromatic hydrocarbon radicals having 1 to 20 C atoms,
  • R 2 R 1 or H with the proviso that at least three radicals R 2 are H, a 5 to 500, preferably 10 to 250, in particular 15 to 75, b 1 to 50, preferably 1 to 20, in particular 3 to 15 , c is 0 to 5, preferably 0 to 1, in particular 0,
  • R 3 independently of one another identical or different, containing at least one double bond hydrocarbon radicals having 2 to 12, preferably 2 to 8, in particular 2 C atoms,
  • organopolysiloxanes of general formula I in at least 6-fold molar excess, based on the double bond-containing siloxane of the general formula II, to give a Si-H groups having Reaction product and further reaction of the reaction product in at least one of the stages
  • the radicals R 1 are preferably identical or different aliphatic or aromatic hydrocarbon radicals having 1 to 20 C atoms, more preferably identical or different unbranched, aliphatic or aromatic hydrocarbon radicals having 1 to 9 C atoms and particularly preferably methyl, ethyl or phenyl.
  • the SiH-group-carrying organopolysiloxane of the general formula I in at least 6-fold molar excess, based on the double bond-containing siloxane of the general formula II, is present it prevents the formation of a network and the formation of highly viscous products comes.
  • they own one of the two aforementioned Method produced organosiloxanes viscosities up to 10,000 mPas.
  • a certain proportion of the organosiloxane may be present in the product in the form of a comb-like modified siloxane.
  • This siloxane framework is retained at the subsequent reaction stages.
  • the preparation of the siloxane polymers can be carried out with solvent or solvent-free.
  • the possibly occurring foaming can be suppressed by the use of solvents.
  • Suitable solvents are, for example, toluene and cyclohexane.
  • Lewis acids preferably boron-containing Lewis acids
  • boron-containing compounds of the catalytic system fluorinated and / or non-fluorinated
  • OrganoborENSen are used, in particular those which are selected from:
  • tris (pentafluorophenyl) borane [CAS no. 1109-15-5]
  • mixtures of the above catalysts it is also possible to use synergistically active compounds. These include salts or complexes, with cations selected from the group of salts of elements of the 4th, 6th, 7th and 8th subgroup and the 4th main group.
  • Alkoxides, acid anions, in particular carboxylates, sulfates, nitrates or phosphates, halides, in particular chlorides, oxides or complexing ligands, in particular acetylacetonate or carbonyls, may preferably be used as amones of the synergistically active compounds of the ka t a 1 ytl s system.
  • Suitable alcohols are, for example, linear or branched, saturated, mono- or polyunsaturated, aromatic, monohydric, monohydric or polyhydric alcohols, polyether monoalcohols, polyetherpolyalcohols,
  • Polyester monoalcohols polyesterpolyalcohols
  • Amino alcohols in particular N-alkyl, arylamino-EO, -PO- alcohols (EO stands for the polyethylene oxide radical, PO for the polypropylene oxide radical), N-alkyl or Arylaminoalkohole and mixtures thereof.
  • EO stands for the polyethylene oxide radical
  • PO for the polypropylene oxide radical
  • N-alkyl or Arylaminoalkohole and mixtures thereof.
  • Process step B) may be the known
  • Hydrosilylation catalysts are used, for
  • Suitable alkenyl / alkynyl compounds are, for example
  • polyethers with double bonds in particular allyl-functional polyethers.
  • the emulsifier systems according to the invention are preferably used as oil-in-water, water-in-oil or water-in-silicone emulsifiers or dispersing aids.
  • the present invention therefore also provides dispersions or emulsions containing at least one of the emulsifier systems according to the invention.
  • the emulsifier system is preferably also used for the production of O / W impregnating emulsions for textiles.
  • the textiles are preferably wet wipers r, particularly preferably moisturizing wipes.
  • the emulsions and dispersions according to the invention contain, based on the total mass, more mass percent of oil component than the sum of the mass percentages of emulsifier, surfactant and optionally co-emulsifier.
  • oil-in-water, water-in-oil and water-in-silicone emulsions and dispersions, as well as O / W impregnating emulsions for textiles, obtained with the aid of the emulsifier systems according to the invention are likewise the subject of Invention.
  • textiles impregnated with O / W impregnating emulsions according to the invention are the subject of the invention. These are characterized by good rejuvenation and a pleasantly velvety, smooth skin feeling.
  • Another object of the invention is the use of emulsifier systems according to the invention for the preparation of cosmetic, dermatological or pharmaceutical formulations.
  • the emulsions and dispersions according to the invention for the preparation of cosmetic, dermatological or pharmaceutical formulations.
  • the cosmetic, dermatological or pharmaceutical formulation containing at least one emulsifier system according to the invention or at least one emulsion or dispersion according to the invention is likewise an object of the invention.
  • Another object of the invention is the use of the emulsifier systems or emulsion or dispersion of the invention for the preparation of optionally dispersed solids containing care and cleaning agents for household or industrial, especially for hard surfaces, leather or textiles.
  • care and cleaning agents for household or industry and the care and cleaning agents for hard surfaces, leather or textiles are also the subject of the invention.
  • the cosmetic, dermatological or pharmaceutical formulations as well as the care and cleaning agents may e.g. contain at least one additional component selected from the group of
  • Emulsifiers and surfactants are Emulsifiers and surfactants.
  • Hydrotropes (or polyols),
  • all cosmetic oils in particular mono- or diesters of linear and / or branched mono- and / or dicarboxylic acids having 2 to 44 carbon atoms with linear and / or branched saturated or unsaturated alcohols having 1 to 22 carbon atoms, can be used.
  • the esterification products of aliphatic, diethylene, alcohols having 2 to 36 carbon atoms with monofunctional aliphatic carboxylic acids having 1 to 22 carbon atoms can be used.
  • long-chain arylic acid esters such as e.g. Esters of benzoic acid, e.g. Benzoic acid esters of linear or branched, saturated or unsaturated alcohols having 1 to 22 carbon atoms, or also isostearyl benzoate or
  • Benzoic acid octyl dodecyl ester Benzoic acid octyl dodecyl ester.
  • Other monoesters suitable as emollients and oil components are e.g. the methyl esters and isopropyl esters of fatty acids having 12 to 22 carbon atoms such as e.g. Methyl laurate, methyl stearate, methyl oleate, methyl thyrogen, isoprolidyl palmitate, isopropenyl, isopropyl stearate, isopropyl oleate.
  • Other suitable monoesters are e.g.
  • Octyldodecyl palmitate, oleyl oleate, oleyl erucate, erucyl oleate, and esters obtained from technical aliphatic alcohol cuts and technical, aliphatic Carboxylic acid mixtures are available, for example, esters of unsaturated fatty alcohols having 12 to 22 carbon atoms and saturated and unsaturated fatty acids having 12 to 22 carbon atoms as they are accessible from animal and vegetable fats. Also suitable, however, are naturally occurring monoester or wax ester mixtures, as present, for example, in jojoba oil or in sperm oil.
  • Suitable dicarboxylic esters are, for example, di-n-butyl adipate, di-n-butyl sebacate, di (2-ethylhexyl) adipate, di (2-hexyldecyl) succinate, diisotridecyl acelate.
  • Suitable diol esters are, for example, ethylene glycol dioleate, ethylene glycol diisotridecanoate, propylene glycol di- (2-ethylhexanoate), butanediol diisostearate, butanediol di-caprylate / caprate and neopentyl glycol di-caprylate.
  • fatty acid esters that can be used as emollients are, for example, C12-15 alkyl benzoate, dicaprylyl carbonate, diethylhexyl carbonate.
  • emollients and oil component are longer chain triglycerides, ie, triple esters of glycerol with three acid molecules, at least one of which is longer chain.
  • fatty acid triglycerides are mentioned; as such, for example, natural, vegetable oils, for example olive oil, sunflower oil, soybean oil, peanut oil, rapeseed oil, almond oil, sesame oil, avocado oil, castor oil, cocoa butter, palm oil but also the liquid portions of coconut oil or palm kernel oil and animal oils such as shark liver oil, cod liver oil, Whale oil, beef tallow and butterfat, waxes such as beeswax, carnauba wax, spermacetol, lanolin and footworm oil, the liquid portions of beef tallow or synthetic triglycerides of caprylic-capric acid mixtures, triglycerides of technical oleic acid, triglycerides with isostearic acid, or of palmitic acid-oleic acid mixtures used as emollients and oil components.
  • natural, vegetable oils for example olive oil, sunflower oil, soybean oil, peanut oil, rapeseed oil, almond oil, sesame oil, avocado oil, castor
  • hydrocarbons in particular also liquid paraffins and isoparaffins are used.
  • examples of usable hydrocarbons are paraffin oil, isohexadecane, polydecene, Vaseline, Paraffinum perliquidum, squalane, ceresin.
  • linear or branched fatty alcohols such as oleyl alcohol or
  • Octyldodecanol as well as fatty alcohol ethers such as dicaprylyl ether can be used.
  • Suitable silicone oils and waxes are, for example, polydimethylsiloxanes, cyclomethylsiloxanes, and also aryl- or alkyl- or alkoxy-substituted polymethylsiloxanes or cyclomethylsiloxanes.
  • Suitable further oil bodies for example, Guerbet alcohols based on fatty alcohols having 6 to 18, preferably atoms 8 to 10 carbon, esters of linear C6-C22 ⁇ fatty acids with linear Ce-C 22 - fatty alcohols, esters of branched C 6 -C 3 -carboxylic acids with linear C6-C22 ⁇ fatty alcohols, esters of linear C6-C 22 -
  • Fatty acids with branched Cs-Cis alcohols in particular 2-ethylhexanol or isononanol, esters of branched C6-C 1 3-carboxylic acids with branched alcohols, in particular 2-ethylhexanol or isononanol, esters of linear and / or branched fatty acids with polyhydric alcohols (for eg
  • Benzoic acid with linear and / or branched C 6 -C 22 -alcohols eg Finsolv TM TN
  • di-alkyl ethers eg Finsolv TM TN
  • emulsifiers or surfactants it is possible to use nonionic, anionic, cationic or amphoteric surfactants.
  • non-ionic emulsifiers or surfactants compounds from at least one of the following groups can be used:
  • Partial esters based on linear, branched, unsaturated or saturated C 6 -C 22 fatty acids, ricinoleic acid and also 12-hydroxystearic acid and glycerol, polyglycerol, pentaerythritol, dipentaerythritol, sugar alcohols (eg sorbitol), alkyl glucosides (eg methyl glucoside, butyl glucoside, lauryl glucoside ) as well as polyglucosides (eg cellulose), mono-, di- and trialkyl phosphates as well as mono-, di- and / or tri-PEG-alkyl phosphates and their salts,
  • alkyl glucosides eg methyl glucoside, butyl glucoside, lauryl glucoside
  • polyglucosides eg cellulose
  • mono-, di- and trialkyl phosphates as well as mono-, di- and / or tri
  • Polysiloxane-polyether copolymers (dimethicone copolyols), w i e z.
  • B. PE G / P PG-20/6 Dimethicone, PEG / PPG-20/20
  • Polysiloxane-polyalkyl-polyether-co-poly-m-epoxy corresponding derivatives e.g. Lauryl or cetyl dimethicone copolyols, especially cetyl PEG / PPG-10/1
  • Citric acid esters such as. Glyceryl Stearate Citrate, Glyceryl Oleate Citrate and Dilauryl Citrate.
  • Anionic emulsifiers or surfactants can be water-solubilizing anionic groups such. a carboxylate,
  • Sulfate, sulfonate or phosphate group and a lipophilic radical are known to the skilled worker in large numbers and are commercially available. These may be alkyl sulfates or alkylphosphates in the form of their alkali, ammonium or
  • cationic emulsifiers and surfactants can be added.
  • quaternary ammonium compounds in particular those provided with at least one linear and / or branched, saturated or unsaturated alkyl chain having 8 to 22 carbon atoms, can be used, such as alkyltrimethylammonium halides such as cetyltrimethylammonium chloride or bromide or behenyltrimethylammonium chloride, but also Dialkyldimethylammonium halides such as distearyldimethylammonium chloride.
  • monoalkylamidoquats such as. Palmitamidopropyltrimethylammonium chloride or corresponding Dialkylamidoquats be used.
  • biodegradable quaternary ester compounds can be used, which may be quaternized fatty acid esters based on mono-, di- or triethanolamine.
  • alkylguanidinium salts may be added as cationic emulsifiers.
  • Typical examples of mild, d. H. are particularly skin-friendly surfactants
  • Substances such as the N-alkyl-N, N-dimethylammonium glycinates for example the Kokosalkyldimethylammoniumglycinat, N-acylaminopropyl-N, N-di me thy 1 ammo niu mg 1 ycinate, for example Kokosacylaminopropyldimethylammoniumglycinat, and 2-alkyl-3-carboxylmethyl-3- Hydroxyethylimidazoline each having 8 to 18 carbon atoms in the alkyl or acyl group and Kokosacylaminoethylhydroxyethylcarboxymethylglycinat.
  • ampholytic surfactants it is possible to use those surface-active compounds which contain, in addition to a C 8/18 alkyl or acyl group in the molecule, at least one free amino group and at least one -COOH or -SO 3 H group and for formation internal salts are capable.
  • ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkylimido derivatives, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids each having about 8 to 18 C atoms in the alkyl group.
  • ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and C12 / 18 acylsarcosine.
  • Suitable thickeners are, for example, polysaccharides, in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, and also higher molecular weight polyethylene glycol mono- and diesters of fatty acids, polyacrylates (eg Carbopol® or Synthalene TM), Polyacrylamides, polyvinyl alcohol and polyvinylpyrrolidone, surfactants such as ethoxylated fatty acid glycerides, esters of fatty acids with polyols such as pentaerythritol or trimethylolpropane, fatty alcohol ethoxylates with narrow homolog distribution or Alkyloligoglucoside and electrolytes such as sodium chloride and ammonium chloride.
  • polysaccharides in particular xanthan gum, guar guar, agar agar, alginates and tyloses,
  • Suitable thickeners for thickening oil phases are all thickeners known to the person skilled in the art.
  • waxes such as hydrogenated castor wax, beeswax or microwax are to be mentioned.
  • inorganic thickeners can be used, such as silica, alumina or phyllosilicates (eg hectorite, laponite, saponite). These inorganic oil phase thickeners may be hydrophobically modified.
  • aerosils, phyllosilicates and / or metal salts of fatty acids, such as, for example, zinc stearate can be used here.
  • viscosity regulators for aqueous surfactant systems e.g. NaCl
  • low molecular weight nonionic surfactants such as Cocoamide DEA / MEA and Laureth-3
  • polymeric, high molecular weight, associative, highly ethoxylated fatty derivatives such as PEG-200 Hydrogenated Glyceryl Palmate.
  • UVB filters for example, organic substances capable of absorbing ultraviolet rays and absorbing the absorbed energy in the form of longer-wave radiation, e.g. Heat again.
  • UVB filters can be oil-soluble or water-soluble.
  • oil-soluble UVB Lichtschut zfil ter are e.g. 3-be n z y 1 i the camphe and its derivatives, e.g. 3- (4-methylbenzylidene) camphor,
  • 4-aminobenzoic acid derivatives e.g.
  • 4- (dimethylamino) benzoic acid esters of cinnamic acid such as 4-methoxycinnamic acid-2-ethylhexyl ester, 4-Methoxycinntklareisopentylester, 2-cyano-3-phenyl-cinnamic acid 2-ethylhexylester (octocrylene), esters of salicylic acid, such as salicylic acid-2 ethylhexyl ester, 4-isopropylbenzyl salicylate, homomenthyl salicylate, benzophenone derivatives, e.g. B.
  • 2-hydroxy-4-methoxybenzophenone 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, esters of benzalmalonic acid, such as di-2-ethylhexy-4-methoxybenzmalonate, Triazine derivatives, such as 2, 4, 6-trianilino (p-carbo-2 '- ethyl-1' hexyloxy) -1, 3, 5-triazine and octyltriazone, propane-1, 3-dione, such as 1 - (4-tert-butylphenyl) -3- (4'-methoxyphenyl) propane-1,3-dione.
  • Suitable water-soluble UVB sunscreen filters are: 2-phenylbenzimidazole-5-s and 1-furfrolyzides and their alkali metal, alkaline earth metal, ammonium, alkylammonium, alkanolammonium and glucammonium salts, sulfonic acid derivatives of benzophenone, e.g. 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid and its salts, sulfonic acid derivatives of the 3-benzylidene camphor, such as e.g. 4- (2-oxo-3-bomylidenemethyl) benzenesulfonic acid and 2-methyl-5- (2-oxo-3-bomylidene) -sulfonic acid and its salts.
  • UVA sunscreen especially derivatives of benzoylmethane come into question, such as l- (4'-tert-butylphenyl) -3- (4 '-methoxyphenyl) propane-1, 3-dione or 1-phenyl-3- (4 '-isopropylphenyl) propane-1,3-di on.
  • UV-A and UV-B filters can also be used in mixtures.
  • insoluble pigments are also suitable for this purpose, namely finely dispersed metal oxides or salts, for example titanium dioxide, zinc oxide, iron oxide, aluminum oxide, cerium oxide, zirconium oxide, silicates (talc), barium sulfate and zinc stearate.
  • the particles should have an average diameter of less than 100 nm, for example between 5 and 50 nm and in particular between 15 and 30 nm. They may have a spherical shape, but it is also possible to use those particles which have an ellipsoidal or otherwise deviating shape from the spherical shape.
  • a relatively new class of light stabilizers are micronised organic pigments such as 2, 2'-methylenebis ⁇ 6- (2H-benzotriazole-2-yl) -4- (1, 1, 3, 3-tetramethylbutyl) -phenol ⁇ with a particle size of ⁇ 200 nm, which is available, for example, as a 50% aqueous dispersion.
  • UV light protection filters can be found in the review by P. Finkel in S ⁇ FW Journal 122, 543 (1996).
  • secondary sunscreen agents of the antioxidant type which interrupt the photochemical reaction chain which is triggered when UV radiation penetrates into the skin.
  • antioxidants e.g. Superoxide dismutase, tocopherols (vitamin E), dibutylhydroxytoluene and ascorbic acid (vitamin C).
  • hydrotropes for example, ethanol, isopropyl alcohol or polyols can be used to improve the flow behavior and the application properties.
  • Polyols contemplated herein may have from 2 to 15 carbon atoms and at least two hydroxyl groups.
  • glycerol alkylene glycols such as, for example, ethylene glycol, diethylene 1-yco-1, propoxy-1-yco-1, butyl-1-narrow-1-yco-1, hexyl-1-yco-1 and also phenyl hy 1 e ng 1 yco 1 e having an average molecular weight of 100 to 1000 daltons, technical oligoglycerine mixtures having an intrinsic degree of condensation of 1.5 to 10 such as technical diglycerine mixtures having a diglycerol content of 40 to 50 wt .-%,
  • MethylolENSen in particular trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol, Niedrigalkylgucoside, in particular those having 1 to 4 carbon atoms in the alkyl radical, such as methyl and Butylglucosid, sugar alcohols having 5 to 12 carbon atoms, such as sorbitol or mannitol, sugars having 5 to 12 carbon atoms, such as glucose or sucrose, amino sugars, such as glucamine.
  • suitable solids are iron oxide pigments, titanium dioxide or zinc oxide particles and those additionally mentioned under "UV protection agents.” It is also possible to use particles which lead to special sensory effects, such as nylon-12, boron nitride, polymer particles such as polyacrylate or Polymethylacrylates 1 atypicals 1 or 1 icone 1 ast ome Reusable fillers include starch and starch derivatives such as tapioca starch, distarch phosphate, aluminum or sodium starch, octenyl succinate and pigments which have neither primary UV filter nor coloring effect For example, Aerosile® (CAS No. 7631-86-9).
  • PVP polyvinylpyrrolidone
  • VA vinyl acetate
  • fat-soluble film-forming agents can be used: z .B.
  • Glycol distearate As pearlescing additives, for example. Glycol distearate or
  • PEG-3 distearate can be used.
  • deodorant active ingredients are, for example, odor maskers such as the usual perfume ingredients, odor absorbers,
  • odor maskers such as the usual perfume ingredients, odor absorbers
  • Germ-inhibiting agents are also suitable for incorporation.
  • Germ-inhibiting substances are, for example, 2,4,4-trichloro-2'-hydroxydiphenyl ether (Irgasan), 1,6-di-
  • basic aluminum chlorides such as aluminum chlorohydrate (“ACH”), and aluminum-zirconium-glycine salts (“ZAG”) can be used as the anhydride on water for ks tof f e.
  • ACH aluminum chlorohydrate
  • ZAG aluminum-zirconium-glycine salts
  • N, N-diethyl-m-toluamide, 1, 2-pentanediol or insect repellent 3535 can be used as insect repellents.
  • Alkylparaben esters may be methylparaben, Ethylparaben, propylparaben and / or Butylparaben act. Instead of phenoxyethanol, other alcohols can be used, such as benzyl alcohol or ethanol.
  • preservatives such as sorbic or benzoic acid, S alicyls acid, 2-bromo-2-nitropropane-l, 3-diol, chloroacetamide, diazolidinyl urea, DMDM hydantoin, Iodopropynyl butylcarbamate, sodium hydroxymethylglycinate, methylisothiazoline, chloromethyl -isothiazoline, ethylhexylglycerol or caprylyl glycol.
  • conditioning agents for example, organic quaternary compounds such as cetrimonium chloride,
  • Distearyldimonium chloride behentrimonium methosulfate, distearoylethyldimonium chloride,
  • Hydroxypropyltrimonium chloride or quaternium-80 or also amine derivatives such as e.g. Aminopropyldimethicone or Stearamidopropyldimethylamine be used.
  • Natural fragrances are extracts of flowers (lily, lavender, roses, jasmine, neroli, ylang-ylang), stems and leaves
  • animal raw materials come into question, such as civet and Castoreum.
  • animal raw materials come into question, such as civet and Castoreum.
  • Fragrance compounds are products of the ester type, Ethers, aldehydes, ketones, alcohols and hydrocarbons. Fragrance compounds of the ester type are, for example, benzyl acetate, phenoxyethyl isobutyrate, p-tert-butylcyclohexyl acetate, vinyl acetate, dimethylbenzylcarbinyl acetate, phenylethyl acetate,
  • Linalyl benzoate benzyl formate, ethyl methyl phenylglycinate, Allylcyclohexylpr opionat, Styrallylpropionat and Benzylsalicylat.
  • the ethers include, for example, benzyl ethyl ether, to the aldehydes, for example, the linear alkanals having 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamen aldehyde, hydrocitronellal, lilial and bourgeonal to the ketones such as the ionone, ⁇ -isomethylionone and methyl cedrylketone to the alcohols include anethole, citronellol, eugenol, isoeugenol, geraniol, linalool, phenylethyl alcohol and terpineol; the hydrocarbons mainly include the terpenes and balsams.
  • fragrances can be used, which together create an appealing scent.
  • Low volatile essential oils which are usually used as aroma components, are suitable as perfumes, such as sage oil, chamomile oil, clove oil, lemon balm oil, mint oil, cinnamon oil, lime blossom oil, Wacho lderbeerenö 1, vetiver oil, Olibanöl, Galbanumöl, Labolanumöl and lavandin oil.
  • cosmetic active ingredients include tocopherol, tocopherol acetate, tocopherol palmitate, ascorbic acid, deoxyribonucleic acid, coenzyme Q10, retinol, bisabolol, allantoin, phytantriol, panthenol, AHA acids, amino acids, hyaluronic acid, alpha-hydroxy acids, polyglutamic acid, creatine (and creatine derivatives), guanidine ( and guanidine derivatives), ceramides, phytosphingosine (and phytosphingosine derivatives), sphingosine (and sphingosine derivatives), pseudoceramides, sphingolipids, essential oils, peptides and oligopeptides, protein hydrolysates, plant extracts and vitamin complexes.
  • ethoxylated glycerol fatty acid esters such as PEG-7 glycerol cocoate
  • cationic polymers such as polyquaternium-7 or polyglycerol esters
  • substances such as lanolin and lecithin as well as polyethoxylated or acylated lanolin and lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides can be used, the latter also serving as foam stabilizers.
  • solvents for example, aliphatic alcohols such as ethanol, propanol or 1, 3-propanediol, cyclic carbonates such as ethylene carbonate, propylene carbonate, glycerol carbonate, esters of mono- or polycarboxylic acids such as ethyl acetate, ethyl lactate, dimethyl adipate and diethyl adipate, propylene glycol, dipropylene glycol, glycerol, glycerol carbonate or Water are used.
  • aliphatic alcohols such as ethanol, propanol or 1, 3-propanediol
  • cyclic carbonates such as ethylene carbonate, propylene carbonate, glycerol carbonate
  • esters of mono- or polycarboxylic acids such as ethyl acetate, ethyl lactate, dimethyl adipate and diethyl adipate
  • propylene glycol dipropylene glycol
  • the cosmetic, dermatological or pharmaceutical formulations according to the invention and the care and cleaning agents contain as additional component pigments (eg TiO 2, FeO x , ZnO, mica and, for example, those listed under UV filter substances and solids) or particles (eg, silicone elastomers, nylon-12, PMMA, boron nitride and, for example, those listed under UV filter substances and solids).
  • pigments eg TiO 2, FeO x , ZnO, mica and, for example, those listed under UV filter substances and solids
  • particles eg, silicone elastomers, nylon-12, PMMA, boron nitride and, for example, those listed under UV filter substances and solids.
  • the cosmetic, dermatological or pharmaceutical formulations according to the invention as well as the care and cleaning agents contain cosmetic active ingredients as an additional component.
  • emulsifier systems according to the invention or of the emulsion or dispersion according to the invention for the preparation of cosmetic or pharmaceutical formulations is preferred.
  • the emulsifier systems according to the invention can be used both in the form of O / W and in the form of O / W emulsifiers.
  • application forms of the emulsions and dispersions containing the emulsifier system of the invention are therefore sprays, lotions, creams, ointments and thus the use over a very wide consistency range of water-thin to strong pasty, in extreme cases even solid, possible.
  • the emulsifier systems may be used in face and body creams and lotions, in sunscreen emulsions, in make-up, in aerosols, blisters, pump sprays, pens, e.g. in the AP / De o area, in baby care products, in intimate care, foot care, hair care, nail care, dental care or oral care products as well as in dermatological ointments.
  • Emulsifier 1 (according to the invention) (O / W emulsifier):
  • Emulsifier 2 (according to the invention) (O / W emulsifier):
  • Emulsifier 3 (according to the invention) (W / O emulsifier) (W / O emulsifier)
  • the structure of the comparative emulsifiers 1 to 5 corresponds to the general formula:
  • Comparative emulsifiers 1-4 correspond to Examples 1-4 of EP 1125574.
  • the emulsions were prepared by the following process: Phases A and B are mixed at room temperature, phase C is added without stirring. The mixture is then homogenized for 1 min. Phases D and E are added, then homogenized again for 1 min.
  • emulsifiers according to the invention have significantly higher stabilizing properties than the comparison emulsifiers 1-4 ( ⁇ - ⁇ -modified siloxanes from EP 1125574) or comparative emulsifier 5 (typical comb-like modified polyether siloxane).
  • Euxyl K 300 (Schulke & Mayr): phenoxyethanol, methylparaben, ethylparaben, propylparaben, butylparaben, isopropylparaben
  • the comparative emulsifiers 1, 2, 4, 5 and 6 (comparative emulsion examples V6-V10) were used as comparative examples.
  • the skin feel of the corresponding emulsion was evaluated in a panel of 10 persons in comparison with the formulation with comparative emulsifier 1, respectively.

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Abstract

L'invention concerne des systèmes émulsifiants contenant des copolymères blocs de siloxane organomodifiés, leur utilisation en particulier pour la production de formulations cosmétiques, dermatologiques ou pharmaceutiques et de produits de soin et de nettoyage, ainsi que les produits obtenus à l'aide de ces systèmes émulsifiants.
EP09745639.6A 2008-05-15 2009-04-15 Utilisation de copolymères blocs de siloxane organomodifiés pour produire des compositions cosmétiques Active EP2273966B1 (fr)

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DE102008001788A DE102008001788A1 (de) 2008-05-15 2008-05-15 Verwendung organomodifizierter Siloxanblockcopolymere zur Herstellung kosmetischer oder pharmazeutischer Zusammensetzungen
PCT/EP2009/054426 WO2009138306A1 (fr) 2008-05-15 2009-04-15 Utilisation de copolymères blocs de siloxane organomodifiés pour produire des compositions cosmétiques ou pharmaceutiques

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JP2011520823A (ja) 2011-07-21
EP2273966B1 (fr) 2018-03-21
BRPI0912561A2 (pt) 2015-10-13
JP5559152B2 (ja) 2014-07-23
CN102026613A (zh) 2011-04-20
DE102008001788A1 (de) 2009-11-26
US8466248B2 (en) 2013-06-18
CA2724414A1 (fr) 2009-11-19
WO2009138306A1 (fr) 2009-11-19
US20110091399A1 (en) 2011-04-21
BRPI0912561B1 (pt) 2016-11-16
CN102026613B (zh) 2013-12-11

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